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CC BY 4.0 · SynOpen 2023; 07(04): 496-500
DOI: 10.1055/a-2176-1585
paper

Cost-Effective and Scalable Synthesis of 4-Bromo-1,2-dimethyl-1H-imidazole: A Key Building Block for Bioactive Molecules

Muthalagu Vetrichelvan  ∗
a   Department of Discovery Synthesis, Biocon Bristol Myers Squibb R&D Centre, Syngene International Ltd., Biocon Park, Plot No. 2 & 3, Jigani Link Road, Bommasandra IV, Bangalore 560 099, India
,
Veeranjaneyulu Lanke
a   Department of Discovery Synthesis, Biocon Bristol Myers Squibb R&D Centre, Syngene International Ltd., Biocon Park, Plot No. 2 & 3, Jigani Link Road, Bommasandra IV, Bangalore 560 099, India
,
Bellam Chandu
a   Department of Discovery Synthesis, Biocon Bristol Myers Squibb R&D Centre, Syngene International Ltd., Biocon Park, Plot No. 2 & 3, Jigani Link Road, Bommasandra IV, Bangalore 560 099, India
,
Arvind Mathur
b   Small Molecule Drug Discovery, Bristol Myers Squibb Research and Early Development, P.O. Box 5400, Princeton, NJ 08543-4000, USA
,
Anuradha Gupta
b   Small Molecule Drug Discovery, Bristol Myers Squibb Research and Early Development, P.O. Box 5400, Princeton, NJ 08543-4000, USA
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Abstract

A cost-effective, scalable, high-yielding, and commercially viable synthesis of 4-bromo-1,2-dimethyl-1H-imidazole (1), an important building block to construct various bioactive molecules has been established. The main feature of this method includes the selection of appropriate starting material 1,2-dimethyl-1H-imidazole in which the existing issue of regioisomer formation is circumvented and the selective debromination is accomplished by using isopropyl magnesium chloride.

Key words

bromination - debromination - imidazole derivative - cost-effective - scalable

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2176-1585.
  • Supporting Information


Publication History

Received: 02 August 2023

Accepted after revision: 08 September 2023

Accepted Manuscript online:
14 September 2023

Article published online:
18 October 2023

© 2023. This is an open access article published by Thieme under the terms of the Creative Commons Attribution License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by/4.0/)

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